Pharmacologic potential of new nitro-compounds as antimicrobial agents against nosocomial pathogens: design, synthesis, and in vitro effectiveness

Andrade, Jéssica Tauany; Alves, Silmara L.G.; Lima, William Gustavo; Sousa, Carla Daiane Ferreira de; Carmo, Lucas Fernandes Do; Sá, Nívea Pereira de; Morais, Fernanda Barbara; Johann, Susana; Villar, José Augusto Ferreira Perez; Ferreira, Jaqueline Maria Siqueira

doi:10.1007/s12223-019-00747-7

Cited by 6 publications

(4 citation statements)

References 44 publications

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“…Nitroarenes are reported to give rise to antimicrobial activity. 54,55 Finally, reactions of polymer 2 with a hydroxylamine derived from pyrene generated polyethylene 6g with a fluorescent functional group that could be utilized in biomedical and waste-sorting applications. 56−58 Although qualitative, we found that this material was fluorescent when irradiated with a conventional UV lamp for visualizing the TLC plates.…”

Section: Synthesis Of Monofunctional Hydroxy-polyethylene 3 By Reduct...mentioning

confidence: 99%

Chemical Modification of Oxidized Polyethylene Enables Access to Functional Polyethylenes with Greater Reuse

Shi,

Ciccia,

Pal

et al. 2023

J. Am. Chem. Soc.

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Polyethylene is a commodity material that is widely used because of its low cost and valuable properties. However, the lack of functional groups in polyethylene limits its use in applications that include adhesives, gas barriers, and plastic blends. The inertness of polyethylene makes it difficult to install groups that would enhance its properties and enable programmed chemical decomposition. To overcome these deficiencies, the installation of pendent functional groups that imbue polyethylene with enhanced properties is an attractive strategy to overcome its inherent limitations. Here, we describe strategies to derivatize oxidized polyethylene that contains both ketones and alcohols to monofunctional variants with bulk properties superior to those of unmodified polyethylene. Iridium-catalyzed transfer dehydrogenation with acetone furnished polyethylenes with only ketones, and ruthenium-catalyzed hydrogenation with hydrogen furnished polyethylenes with only alcohols. We demonstrate that the ratio of these functional groups can be controlled by reduction with stoichiometric hydride-containing reagents. The ketones and alcohols serve as sites to introduce esters and oximes onto the polymer, thereby improving surface and bulk properties over those of polyethylene. These esters and oximes were removed by hydrolysis to regenerate the original oxygenated polyethylenes, showing how functionalization can lead to materials with circularity. Waste polyethylenes were equally amenable to oxidative functionalization and derivatization of the oxidized material, showing that this low- or negative-value feedstock can be used to prepare materials of higher value. Finally, the derivatized polymers with distinct solubilities were separated from mechanically mixed plastic blends by selective dissolution, demonstrating that functionalization can lead to novel approaches for distinguishing and separating polymers from a mixture.

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Section: Synthesis Of Monofunctional Hydroxy-polyethylene 3 By Reduct...mentioning

confidence: 99%

Chemical Modification of Oxidized Polyethylene Enables Access to Functional Polyethylenes with Greater Reuse

Shi,

Ciccia,

Pal

et al. 2023

J. Am. Chem. Soc.

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“…Among the compounds with significant pharmacological activities, compounds containing a nitro group are highlighted because they have an important pharmacophoric functionality in their molecules, which facilitates their use in medicinal and therapeutic applications. Nitro‐derivatives are associated with several biological activities including anti‐inflammatory, [ 39 ] antitumor, [ 40 ] antimicrobial, [ 41 ] and antileishmanial [ 42 ] activities. To ascertain the effect of the nitro group at position 3, we planned to synthesize nitro product 3 by nitration of compound 2 with a mixture of fuming nitric acid and sulfuric acid in acetic acid (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, anticancer evaluation, and molecular docking study of novel 4‐hydroxybenzo[h][1,6]naphthyridine‐2,5‐dione derivatives

Mostafa

2022

J of Physical Organic Chem

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An operationally efficient and affordable lactone-to-lactam transformation was designed from pyrano [3,2-c]quinolinone 1 to obtain 4-hydroxybenzo [h][1,6] naphthyridine-2,5-dione 2 utilizing ammonium acetate. The newly synthesized compound 2 was subjected to different electrophilic substitution reactions such as nitration, chlorination, bromination, and N-acylation to obtain novel benzo [h][1,6]naphthyridine derivatives with different substituents at C-3, C-4, and NH. Structures of novel products were achieved by elemental analyses and spectroscopic techniques. The benzonapthyridine derivatives were screened for their antitumor activities against some cancer cell lines including HepG-2, HCT-116, and MCF-7. All the examined compounds revealed strong, good, moderate to weak anticancer activity compared with 5-fluorouracil as a reference standard. Compound (3, -3NO 2 ) was the most cytotoxic one and exhibited a higher inhibitory activity than the standard drug against HCT-116 and MCF-7 with IC 50 values of 20.7 ± 1.9 and 22.5 ± 2.1 μg/ml, respectively, and strong activity against HepG-2 with IC 50 = 15.3 ± 0.7 μg/ml. Moreover, a molecular docking study was carried out for the tested compounds against the crystallographic structure of the Topo II enzyme as a potential target to investigate their binding modes. Docking results showed that compound 6b fitted well into the active site of topoisomerase II (PDB ID: 1ZXM) with hydrogen bond interactions.

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“…In this context, researchers synthesized several nitro derivatives through an oxa-Michael-aldol condensation reaction and tested their potential antimicrobial activity against Staphylococcus aureus and Candida sp, two main microorganisms involved in frequent nosocomial infections (Figure 5). Experimental results indicated that nitro derivatives with some degree of halogenation 9b-9d had the best results with minimum inhibitory concentration (MIC) in the range of 15.6-62.5 μg/mL for S. aureus and minimum fungicidal concentration (MFC) 15-500 62.5 μg/mL in the case of Candida [27]. There is an increasing interest in developing new antimicrobial agents not only because of the growing resistance to antibiotics but also because of the risk of nosocomial infections (infectious diseases acquired within a hospital).…”

Section: Antibacterialmentioning

confidence: 99%

“…Nitroderivatines containing one F and/or two Cl atoms showed the best activity against S. aureus (15.6-62.5 µg/mL) and Candida sp. (15-500 62.5 µg/mL), respectively[27].…”

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confidence: 97%

The Diverse Biological Activity of Recently Synthesized Nitro Compounds

et al. 2022

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The search for new and efficient pharmaceuticals is a constant struggle for medicinal chemists. New substances are needed in order to treat different pathologies affecting the health of humans and animals, and these new compounds should be safe, effective and have the fewest side effects possible. Some functional groups are known for having biological activity; in this matter, the nitro group (NO2) is an efficient scaffold when synthesizing new bioactive molecules. Nitro compounds display a wide spectrum of activities that include antineoplastic, antibiotic, antihypertensive, antiparasitic, tranquilizers and even herbicides, among many others. Most nitro molecules exhibit antimicrobial activity, and several of the compounds mentioned in this review may be further studied as lead compounds for the treatment of H. pylori, P. aeruginosa, M. tuberculosis and S. mutans infections, among others. The NO2 moiety triggers redox reactions within cells causing toxicity and the posterior death of microorganisms, not only bacteria but also multicellular organisms such as parasites. The same effect may be present in humans as well, so the nitro groups can be considered both a pharmacophore and a toxicophore at the same time. The role of the nitro group itself also has a deep effect on the polarity and electronic properties of the resulting molecules, and hence favors interactions with some amino acids in proteins. For these reasons, it is fundamental to analyze the recently synthesized nitro molecules that show any potential activity in order to develop new pharmacological treatments that enhance human health.

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Pharmacologic potential of new nitro-compounds as antimicrobial agents against nosocomial pathogens: design, synthesis, and in vitro effectiveness

Cited by 6 publications

References 44 publications

Chemical Modification of Oxidized Polyethylene Enables Access to Functional Polyethylenes with Greater Reuse

Chemical Modification of Oxidized Polyethylene Enables Access to Functional Polyethylenes with Greater Reuse

Synthesis, anticancer evaluation, and molecular docking study of novel 4‐hydroxybenzo[h][1,6]naphthyridine‐2,5‐dione derivatives

The Diverse Biological Activity of Recently Synthesized Nitro Compounds

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